I tackled this challenge from two sides. First, I wanted the outfit to be a reflection of the holiday season. Second, each item was also chosen for its practicality.
Part I: The Look
I first saw the green plaid with red turtleneck combination on Blair and loved how festive it looked. Then when Khatu wore it, I told myself that I must re-create it for this holiday season. Turns out, there's no better time than for this challenge.
I think this colorful combination would contrast nicely against white bottoms. White jeans were my first choice and a white wool mini skirt was a close second. Since I own neither, I made do with what I had and wore a white cotton skirt.
Part II: The Logistics
Turtleneck + tights: Friends who have gone to sales without dressing rooms (such as Barney's Warehouse sale or Running of the Brides @ Filene's Basement) have all shared stories that wearing a tank top with leggings is the way to go. Both pieces are form-fitting and act like a second layer of skin, so it's easy to slip on clothes to try on while still able to gauge fit. Although those were more extreme shopping conditions, I wouldn't hesitate to adopt the same philosophy when I'm out shopping regularly. The tank top with leggings equivalent for winter is a turtleneck and tights. Chances are, most clothes I try on won't require the removal of this base layer, so I can stay warm and be my usual lazy self (no need to constantly remove and put on layers in the dressing room).
Shirt: An extra layer for warmth that I could possibly do without, or swapped for a sweater.
Flats: Comfortable flat shoes are a must for walking and standing on my feet for extended periods of time.
Coat: To reduce the bulkiness a bit, I chose a short coat over a long coat. It's easier to maneuver around in and also not as heavy to carry if I decide to take it off indoors.
Bag:: Roomy enough to store potential cold weather accessories (ie: hat, scarves, gloves) and with long handles so it can be worn over the shoulder to free up both hands to better peruse items.
sunglasses: Walmart aviator (similar)
jacket: J.Crew Majesty peacoat (this season's sold here)
shirt: Gap fitted boyfriend flannel ruffle shirt (sold here)
turtleneck: J.Crew Factory tissue turtleneck tee (sold here)
skirt: Express (similar)
tights: J.Crew (sold here)